Startup Life: Unscripted #34 with Dominic DeWalt, Business Strategy & Operations Lead at Mermaid Chart

Startup Life: Unscripted is a TNG Media newsletter, as part of The Nudge Group, where we feature candid conversations with startup operators about their career journeys and experiences. If you received this email as a forward, you can read all our past interviews and subscribe right here.

Welcome back to Startup Life: Unscripted! This week, we're chatting with Dominic DeWalt, who went from landing Watson Living in Forbes and WSJ as an intern to tackling the startup scene head-on at Mermaid Chart. Dominic shares his experiences, the ups and downs of working in startups, the variety of roles he's juggled, and the key takeaways from his journey.

Key interview takeaways:

🔄 Career Transitions: From public companies to startups, Dominic discusses what draws him back to the startup ecosystem and how these varied experiences shape his approach at Mermaid Chart.

🎩 Wearing Multiple Hats: He sheds light on juggling diverse roles within a startup, from operations to marketing and beyond, offering insights into his organisational strategies.

🌟 Mentorship Impact: Dominic highlights the role of mentorship in his career, particularly the guidance from Andy, CEO of Mermaid Chart, that has propelled his growth.

🚀 For Aspiring Startup Enthusiasts: Dominic shares invaluable advice for those looking to dive into the startup world, stressing the importance of learning, adaptability, and the right mindset for tackling new challenges.

Hey Dominic, kicking things off with a bang at Watson Living by getting featured in Forbes and the WSJ is no small feat! Can you share what that experience was like for you, especially as an intern? Could you let us in on how you managed to grab that high-profile press attention?

When I began at Watson Living, a rental rewards startup, I had come in as a sales and marketing intern. I was the 6th person on the team so there were a lot of really exciting opportunities for me to make an impact in my internship!

Getting Watson in the press was one of my first projects and it gave me a true taste of how the real world works and how to approach it. Spoiler, getting over the analysis paralysis and just taking some action will get you a long way!

I tried to approach this project in a targeted and personal way as all my research had shown that reporters are busy and you have to personalise everything if you want to get their attention. I started by finding as many publications that could be relevant to our business in the proptech space.

Once I had this list, I began scouring these sites for any articles that report on problems that would be similar to the problems we solved at Watson. As I read these articles, I began collecting a massive list of the authors so that I could find reporters who would actually be interested in covering us.

This became my "high value target" list that I began reaching out to. Since I was familiar with their work now, writing a personalised email became a lot easier. I started by making an email template with a standard pitch of what we were hoping to have a reporter cover and I included one sentence that commented on some of their previous work.

I tried to avoid just blatant headline personalization and would try to mention something specific that they wrote in the past. Recognizing someone's hard work is a really great way to kick off a conversation! I not only emailed these reporters, I messaged them on LinkedIn, sent in messages from the "contact us" form on the websites and exhausted all channels. I wanted to make sure we at least got in front of them! 

Many reporters never got back to me, but all you really need is one or two. Luckily, I had connected with a reporter at the WSJ on LinkedIn through my outreach and she was interested in learning more. This particular author had written many articles on proptech companies and she was the perfect person to cover us.

It was fate that our solution at Watson Living matched up perfectly with her career focus! At the same time, I had also connected with another reporter at Forbes who was eager to interview the founder. I made these intros and the process began. I had previously written a press release that the founder iterated on and used for these conversations too.

I definitely can't take all the credit as I didn't drive the interviews home, but I was able to make such a huge impact from the work I had put in that I was really hooked on the startup life from that point on! It was incredibly invigorating when I woke up in my tiny college apartment and saw Watson Living posted in the Wall Street Journal. This definitely helped eliminate any fear I had for tackling new projects that the founder would throw at me. 

Transitioning from a seed-stage startup to a public company like Appfolio, and then back into the startup world with Mermaid Chart, you've seen quite a spectrum of company stages and sizes. How do these experiences compare, and what draws you back to the startup scene?

I know startups aren't for everyone, but I love the chaos and diverse work that I get involved in. Going from Watson where I was able to have my hands in nearly everything, I found that going to a larger public company really siloes your experience to your job title.

Appfolio was a really awesome company and I actually moved down to Santa Barbara to work in their office since all my previous experience was remote. On-site allows you to really connect with your coworkers and the fact that Appfolio was a 'tech' company made it all the better. They really wine and dine their employees in the office with free snacks, happy hours, lunches, you name it. This was such a cushy lifestyle and I learned a lot about how to think analytically while I was a business systems analyst there. 

Overall, the public company work provided a fantastic work life balance, but I didn't like the linear growth path that I'd be confined to. This means I would be in my role as a Business systems analyst, then possibly promoted to a senior business systems analyst, then eventually a lead business systems analyst, then maybe a manager way down the road.

Each step didn't have very different responsibilities and when I got the opportunity to work with Andy again, the founder of Watson, I knew I had to jump on it. He had become the CEO of Mermaid Chart and it was only him and 8 software engineers. He needed some help on the business side and the company was primed for some great growth. It's pretty hard to say no to a title bump, more exciting work, and the ability to grow so much faster.

I didn't hesitate long and now I'm celebrating my 3 and half month mark at Mermaid Chart! So far I've gotten the opportunity to lead product management and growth which are things I never would have had experience with if I didn't make the jump back into startups. 

Wearing multiple hats is a startup staple. Could you give us a glimpse into how you juggle operations, marketing, and product management all in one go? Any tools or strategies that keep you on track?

The key for me is to always keep organised and take notes on everything. Startups are so chaotic that so many things can fall through the cracks. To ensure that I can properly tend to ops, marketing, and product management I keep a daily to-do list that also contains a backlog so I can put more things in if I'm really efficient that particular day. I love Notion and I think everyone should ditch Google docs and give it a try. This is where I centralise my to dos, notes, and absolutely everything. 

When I'm in meetings or interviewing customers I'll take notes on everything and immediately following that meeting, I'll synthesise the action items from the notes I took. These action items then go directly in my to do list that I'll organise every Monday. This works really well for me because I will never let anything fall through the cracks and can become a reliable team member that others can count on. 

There are some potential downfalls to this strategy since sometimes the number of action items can really get out of hand as business expands. At this point, communication and prioritisation are most important. Every Monday I send a message to the CEO with my intended priorities for the week. This is so he has an understanding of how full my plate is and so that he can help me reprioritise if needed.

This clear communication really helps me from getting overwhelmed because I know that he understands where my focus and time is being dedicated. For example, if I'm prioritising advertisements for one week, he'll know that I won't be focusing on the product and there aren't any unrealistic expectations. If this is misaligned then he easily shoots me a message to reorder my priorities and then I'm off to the races for that week!

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The startup world moves fast, with lots of twists and turns along the way. Could you tell us about a recent hurdle Mermaid Chart came across and how you dealt with it? What did you learn from going through that?

Absolutely! I'm only 3 and a half months in so I'm sure some bigger challenges are looming on the horizon, but I'd love to share a challenge we've faced internally. 

Mermaid Chart was a unique challenge for me when I first joined as the entire company is remote and dispersed globally. We have engineers in Sweden, India, the UK, and the US. The timezone challenge is difficult as I'm in California and I was also coming in as a first time product manager.

There were a lot of gaps in how the team worked together, prioritised development, and actually worked through sprints. This was a huge challenge because I've had no experience with the development cycle and how each part plays with the other. I began heavily researching product processes and agile development so that I could help get the team on track and developing efficiently. 

I wrote this whole plan for our product development process and began implementing it with the team, but one thing I didn't account for is that people are actually people and have their own work styles that you have to account for and support. Some people work really great with ambiguous direction and others don't.

Everybody has their own comfortability with Jira tickets and how they develop off the back of them. I realised that the product process I was building was great in theory, but I needed to adapt it to what actually works for our team. This is still an iterative process but I'm feeling really great about where we're headed! This really gave me a better look into the people management side of startups and I can tell that I'm going to continue to learn a lot more over time.

Mentorship seems to play a big role in your career. How has working closely with Andy shaped your approach to startup life, and what's one piece of advice from him that's been a game-changer for you?

Andy has not only been my boss, but my greatest supporter so far in my career. It's really great when those two things match up! Every month we'll have a career development chat where I can ask him any question and get his advice.

I think my biggest learning so far, besides the actual business knowledge and insight he's given me, is to keep it simple. It's really cliche, but I tend to overthink some things and write paragraphs about these really detailed plans that sometimes go down the wrong path.

When I send him these huge ideas, he'll just reply with 2-3 sentences highlighting a much simpler path that always comes out as much more approachable. Don't create a monster for yourself and let's just keep it simple. 

With a team as spread out as Mermaid Chart's, fostering unity and collaboration must take some creative strategies. What are your go-to methods for keeping everyone on the same page and pushing forward together?

Like I said a little earlier, this is a big challenge. Asynchronous work is something everyone is still trying to figure out from a culture standpoint.

Communication is obviously really key here, but I love to take Loom videos that explain context and the problems that need solving so that when I'm off sleeping through the night, they should have as much information as possible to keep us all aligned. We have about an hour in the morning where our work days align so my 8-9 am is almost always booked. That live connection is super important if you can achieve it. 

Another thing from a more general standpoint is that I think recognition is really motivating. I try to send exciting business updates to the team as I see them. Our growth has been going pretty well so I love calling out new record sign ups or goal achievements.

I think these types of updates are helpful and at the same time I highlight that it's THEIR work that's delighting customers. It's not just code that the team is writing, it's real people that they're effecting in a positive way. This type of recognition always motivates me so I really hope my team agrees haha!

Reflecting on your journey so far, what advice would you give to young professionals eager to dive into the startup world? Are there any specific skills or mindsets you believe are critical for success in such a fast-paced environment?

I think the biggest skill anyone can have in the startup environment is being good at learning. While in school you always think that everyone in the workforce is an expert and they have skills that you don't have.

While some of this is true, I really believe that you can learn anything so do not be afraid to tackle new challenges. Always say yes to new projects (within reason) because that path may open up a lot of doors for you.

I'll also continue to harp on keeping organised, taking good notes, and becoming reliable. The best mindset is "yes I can" because you can definitely learn something new and apply it.

Trust yourself, be confident in your abilities to learn new things and then you'll never be hesitant to tackle new challenges and approach opportunities. I'm always open to expanding more so feel free to connect with me on LinkedIn at any time!

From the Startup Life team

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